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Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

Identifieur interne : 003172 ( PubMed/Curation ); précédent : 003171; suivant : 003173

Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

Auteurs : Joseph Salamoun [États-Unis] ; Shelby Anderson ; James C. Burnett ; Rick Gussio ; Peter Wipf

Source :

Organic letters [ 1523-7052 ] ; 2014.

RBID : pubmed:24641272

Descripteurs français

KwdFr :
- Acides boroniques (), Antinéoplasiques (), Antinéoplasiques (synthèse chimique), Antinéoplasiques (toxicité), Catalyse, Chimie organique (), Composés hétérocycliques (), Composés hétérocycliques (synthèse chimique), Composés hétérocycliques (toxicité), Furanes (), Humains, Oxazoles (), Palladium (), Relation structure-activité, Structure moléculaire, Tests de criblage d'agents antitumoraux.
MESH :
- synthèse chimique : Antinéoplasiques, Composés hétérocycliques.
- toxicité : Antinéoplasiques, Composés hétérocycliques.
- Acides boroniques, Antinéoplasiques, Catalyse, Chimie organique, Composés hétérocycliques, Furanes, Humains, Oxazoles, Palladium, Relation structure-activité, Structure moléculaire, Tests de criblage d'agents antitumoraux.

English descriptors

KwdEn :
- Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (chemistry), Antineoplastic Agents (toxicity), Boronic Acids (chemistry), Catalysis, Chemistry, Organic (methods), Drug Screening Assays, Antitumor, Furans (chemistry), Heterocyclic Compounds (chemical synthesis), Heterocyclic Compounds (chemistry), Heterocyclic Compounds (toxicity), Humans, Molecular Structure, Oxazoles (chemistry), Palladium (chemistry), Structure-Activity Relationship.
MESH :
- chemical , chemical synthesis : Antineoplastic Agents, Heterocyclic Compounds.
- chemical , chemistry : Antineoplastic Agents, Boronic Acids, Furans, Heterocyclic Compounds, Oxazoles, Palladium.
- chemical , toxicity : Antineoplastic Agents, Heterocyclic Compounds.
- methods : Chemistry, Organic.
- Catalysis, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Structure-Activity Relationship.

Abstract

Two complementary approaches for the preparation of linked 5-membered heterocycles were developed. The Pd-catalyzed Suzuki-Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to higher overall yields, but C,H-bond activation was a more efficient strategy for the coupling at C(2) of oxazoles. Potency and selectivity of the final hydroxymethyl products in renal (A498), lung (NCI-H226), kidney (CAKI-1), and breast (MDA-MB-468, MCF7) carcinoma cell lines were determined.

DOI: 10.1021/ol500620m
PubMed: 24641272

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Le document en format XML

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<term>Boronic Acids (chemistry)</term>
<term>Catalysis</term>
<term>Chemistry, Organic (methods)</term>
<term>Drug Screening Assays, Antitumor</term>
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<term>Heterocyclic Compounds (chemical synthesis)</term>
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<term>Molecular Structure</term>
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<term>Antinéoplasiques ()</term>
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<term>Antinéoplasiques (toxicité)</term>
<term>Catalyse</term>
<term>Chimie organique ()</term>
<term>Composés hétérocycliques ()</term>
<term>Composés hétérocycliques (synthèse chimique)</term>
<term>Composés hétérocycliques (toxicité)</term>
<term>Furanes ()</term>
<term>Humains</term>
<term>Oxazoles ()</term>
<term>Palladium ()</term>
<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
<term>Tests de criblage d'agents antitumoraux</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antineoplastic Agents</term>
<term>Heterocyclic Compounds</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antineoplastic Agents</term>
<term>Boronic Acids</term>
<term>Furans</term>
<term>Heterocyclic Compounds</term>
<term>Oxazoles</term>
<term>Palladium</term>
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<term>Composés hétérocycliques</term>
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<term>Humains</term>
<term>Oxazoles</term>
<term>Palladium</term>
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<term>Tests de criblage d'agents antitumoraux</term>
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<front><div type="abstract" xml:lang="en">Two complementary approaches for the preparation of linked 5-membered heterocycles were developed. The Pd-catalyzed Suzuki-Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to higher overall yields, but C,H-bond activation was a more efficient strategy for the coupling at C(2) of oxazoles. Potency and selectivity of the final hydroxymethyl products in renal (A498), lung (NCI-H226), kidney (CAKI-1), and breast (MDA-MB-468, MCF7) carcinoma cell lines were determined.</div>
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Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

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